Childhood Love Never Dies: Milo of the Phantom Tollbooth

The introduction to my brooding young crush is as follows:

“There once was a boy named Milo who didn’t know what to do with himself. Not just sometimes, but always.”

From two sentences, my 11-year-old self (jaded and indifferent beyond my years) was in love. Thirteen years later, my childhood heart is still captive to the formerly-apathetic star of Norton Juster’s The Phantom Tollbooth. Now, I know what you’re thinking: isn’t that kind of creepy? Yes. And no.

Milo, probably a preteen himself, is the perfect blend of melancholy and brooding that any girl would fall for. He starts off the novel with the kind of detachment from the world that makes girls give long sighs and stare dreamily at the back of his head during World History class. He is, perhaps, the only child who looks at a surprise gift and declares “[m]ost probably I won’t like it anyway”. Spoiler alert: He ends up liking it.

The surprise package, whose messenger remains unknown even by the end of the novel, is for all intents and purposes a magical tollbooth (and car) that transports Milo into another dimension… universe, world… place, called The Lands Beyond. We’re not quite sure how he gets there, other than at the end of chapter one he drives through the tollbooth, and the beginning of chapter two finds him “[s]uddenly… speeding along unfamiliar country highway.” As the highway takes him through a series of bizarre adventures (which all act, in true childhood story form, to teach a lesson of some kind) Milo begins to change. His environment, and the creatures he meets along the way, shape his outlook on life and slowly begin to chip away at the hard apathetic exterior he has carefully crafted in his few years of life.

What makes Milo so endearing is the process he goes through in order to change. There is no grand battle, no dragon to be slain. Each adventure is subtle and slow, and requires a gradual transformation in Milo’s perspective and attitudes. The lessons serve, as such, to peel back the layers of Milo’s character revealing more than just disenchantedness and ennui. Milo begins to develop attachments to the characters that accompany him on the larger task of retrieving the princesses Rhyme and Reason in order to unite the kingdom. (I did say this was a children’s story, right?)

Milo’s physical appearance, accompanied by the pen sketches sprinkled throughout the novel, is a bit odd to say the least. His head looks rather big, and his nose is very pointed. I’m not quite sure what to even say about his hair, but that is perhaps all for the better. Love for Milo stems from his development throughout the book – from that first moment of deep, “artsy” brooding, to the bonds he slowly develops for his companions (a Humbug and a time-keeping dog named Tock), all the way to his exemplary bravery in rescuing the princesses. He even gains a strange, sarcastic sense of humor. When the merry band of rescuers are facing certain peril, and there seems to be no way out, Milo cheekily chirps to Tock, “Well time flies doesn’t it?” And they proceed to fly away on the dog. What girl doesn’t love a sense of humor?

Milo also isn’t afraid of his emotions. By the end of the novel, he expresses deep sadness at leaving his friends behind as he has to return to Earth… or the real world… home. When he realizes that the tollbooth has been removed (after all, there are countless other pessimistic and depressed 11-year-olds in need of a good dose of magic) he becomes momentarily filled with despair, but then realizes that surrounding him is a beautiful world, and hundreds of books to take him on whatever adventure he would want (wink wink, nudge nudge). It is this moment that seals Milo’s maturation.

I imagine, were Milo to grow up, he’d be that very attractive almost-hipster guy in your English Lit class who read The Canterbury Tales for fun, and wore tweed jackets in a non-ironic way; who looks a bit like Hugh Dancy in Hannibal. The kind of guy who has that old melancholy hiding beneath his eyes, but is so overwhelmed by appreciation for the world around him that the sadness is masked by a childlike spark of wonderment and curiosity. For myself, and my fellow gen-Y-ers, who better to crush on than someone who manages to claw his way out of cynicism?

So no, it isn’t creepy that I, at 24 years old, still hold a special place in my heart for Milo. Maybe, just maybe, it’s less creepy now.